LITHIUM AMIDE

Lithium amide (LiNH2) is an amide of an alkali metal with lithium atoms having larger positive charges than hydrogen atoms. 
Lithium amide or lithium azanide is an inorganic compound with the chemical formula LiNH2. 
Lithium amide is a white solid with a tetragonal crystal structure.

CAS Number: 7782-89-0
EC Number: 231-968-4
Chemical Formula: LiNH2
Molar Mass: 22.96 g·mol−1

Lithium amide is a cholesterol ester transfer inhibitor that is used to treat infectious diseases. 
Lithium amide prevents the accumulation of cholesterol in the brain and other tissues. 

Lithium amide has been shown to inhibit bacterial growth by binding to DNA-dependent RNA polymerase, thereby preventing transcription and replication. 
The high frequency of human activity has been shown using a patch-clamp technique on human erythrocytes. 

This active form is metabolized through a number of metabolic transformations, including hydrolysis by esterases or glucuronidases, oxidation by cytochrome P450 enzymes, reduction by glutathione reductase, or conjugation with glucuronic acid. 
Lithium amide also specifically binds to markers expressed at high levels in Mycobacterium tuberculosis strains (e.g., ESX-1 secretion system protein) and inhibits cell growth in culture.

Lithium amide (LiNH2) is an amide of an alkali metal with lithium atoms having larger positive charges than hydrogen atoms. 
Lithium amide is a moisture-sensitive molecule that converts to LiOH and NH3 on reaction with H2O. 
Lithium amide is majorly used in hydrogen storage applications.

Lithium Amide is a colorless to gray crystal or powder with an Ammonia odor. 
Lithium amide is used to make drugs, in chemical manufacturing, and as a catalyst. 

Lithium Amide is generally immediately available in most volumes. 
High purity, submicron and nanopowder forms may be considered. 

Lithium amide is a white crystalline powder with an odor of ammonia. 

Lithium amide or lithium azanide is an inorganic compound with the chemical formula LiNH2. 
Lithium amide is a white solid with a tetragonal crystal structure.

Lithium amide can be made by treating lithium metal with liquid ammonia:
2 Li + 2 NH3 → 2 LiNH2 + H2

Other lithium amides:
The conjugate bases of amines are known as amides. 
Thus, a lithium amide may also refer to any compound in the class of the lithium salt of an amine. 

These compounds have the general form LiNR2, with the chemical lithium amide itself as the parent structure. 
Common lithium amides include lithium diisopropylamide (LDA), lithium tetramethylpiperidide (LiTMP), and lithium hexamethyldisilazide (LiHMDS). 

They are produced by the reaction of Li metal with the appropriate amine:
2 Li + 2 R2NH → 2 LiNR2 + H2

Lithium amides are very reactive compounds. 
Specifically, they are strong bases.

Examples:
Lithium tetramethylpiperidide has been crystallised as a tetramer.
On the other hand, the lithium derivative of bis(1-phenylethyl)amine crystallises as a trimer.

Lithium amide is also possible to make mixed oligomers of metal alkoxides and amides.
These are related to the superbases, which are mixtures of metal alkoxides and alkyls. 
The cyclic oligomers form when the nitrogen of the amide forms a sigma bond to a lithium, while the nitrogen lone pair binds to another metal centre.

Other organolithium compounds (such as BuLi) are generally considered to exist in and function via high-order, aggregated species.

Applications of Lithium amide:
Lithium amide is used in the preparation of active pharmaceutical ingredients and antioxidants. 
Lithium amide acts as a catalyst for polymers, as nucleophiles and as strong bases. 

Lithium amide serves as a reagent in the synthesis of antiinflamatory and preoresolving protectin D1, chemotype dipeptidyl peptidase IV inhibitors and sterically congested triarylamines. 
Lithium amide finds application in dyes displaying large stokes shifts. 
In addition to this, Lithium amide is used as a reagent for cross-coupling of aryl chlorides and amine.

Reagent for synthesis of:
Antiinflamatory and preoresolving protectin D1
Chemotype dipeptidyl peptidase IV inhibitors

Sterically congested triarylamines
Dyes displaying large Stokes shifts

GM1 ganglioside derivatives
Reagent for cross-coupling of aryl chlorides and amines

Uses of Lithium amide:
Lithium amide is used in the production of pharmaceuticals and antioxidants.
Lithium amide is used as a catalyst for polymers and other chemical synthesis.

Lithium amide is used in production of antioxidants and antihistamines
Lithium amide is now used in many reactions in preference to sodium amide for safety reasons, and because Lithium amide often shows greater selectivity.

Industrial Processes with risk of exposure:
Plastic Composites Manufacturing

Manufacturing Methods of Lithium amide:
Lithium amide is produced industrially by heating lithium metal or lithium hydride in a stream of ammonia. 
Lithium amide also forms slowly when lithium metal dissolves in liquid ammonia.

Lithium amide is produced from the reaction of anhydrous ammonia and lithium hydride.

Stability and Reactivity of Lithium amide:

Reactivity:
Powdered LITHIUM AMIDE is highly reactive. 
A strong base. 

Reacts to release toxic ammonia gas with water. 
Forms explosive peroxide on storage.

Chemical stability:
Reacts violently with water, Moisture sensitive, Air sensitive. 

Possibility of hazardous reactions:
Hazardous Polymerization No information available. 
Hazardous Reactions No information available. 

Conditions to avoid:
Excess heat. 
Exposure to air. 

Incompatible products. 
Exposure to moist air or water

Incompatible materials:
Acids. 
Water. 

Strong oxidizing agents. 
Alcohols. 

Hazardous decomposition products:
Nitrogen oxides (NOx). 
Thermal decomposition can lead to release of irritatinggasesandvapors. 

Carbon monoxide (CO). 
Carbon dioxide (CO2). 

Ammonia. 
Hydrogen.

Handling and Storage of Lithium amide:
Prior to working with Lithium Amide you should be trained on Lithium amide proper handling and storage.
Contact with WATER or MOIST AIR may form flammable and poisonous gases.
Lithium Amide is not compatible with OXIDIZING AGENTS (such as PERCHLORATES, PEROXIDES, PERMANGANATES, CHLORATES, NITRATES, CHLORINE, BROMINE and FLUORINE); STRONG ACIDS (such as HYDROCHLORIC, SULFURIC and NITRIC); and ALCOHOLS.

Store in tightly closed containers in a cool, well-ventilated area away from HEAT and LIGHT.
Sources of ignition, such as smoking and open flames, are prohibited where Lithium Amide is used, handled, or stored.

Metal containers involving the transfer of Lithium Amide should be grounded and bonded.

Use only non-sparking tools and equipment, especially when opening and closing containers of Lithium Amide.
Wherever Lithium Amide is used, handled, manufactured, or stored, use explosion-proof electrical equipment and fittings. 

Nonfire Spill Response:
ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. 
Do not touch or walk through spilled material. 

Stop leak if you can do Lithium amide without risk. 
DO NOT GET WATER on spilled substance or inside containers. 

Use water spray to reduce vapors or divert vapor cloud drift. 
Avoid allowing water runoff to contact spilled material. 
FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors. 

SMALL SPILL: 
Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. 
Dike for later disposal; do not apply water unless directed to do so. 

POWDER SPILL: 
Cover powder spill with plastic sheet or tarp to minimize spreading and keep powder dry. 
DO NOT CLEAN-UP OR DISPOSE OF, EXCEPT UNDER SUPERVISION OF A SPECIALIST.

First Aid Measures of Lithium amide:
Call 911 or emergency medical service. 
Ensure that medical personnel are aware of Lithium amide(s) involved and take precautions to protect themselves. 

Move victim to fresh air if Lithium amide can be done safely. 
Give artificial respiration if victim is not breathing. 

Do not perform mouth-to-mouth resuscitation if victim ingested or inhaled Lithium amide; wash face and mouth before giving artificial respiration. 
Use a pocket mask equipped with a one-way valve or other proper respiratory medical device. 

Administer oxygen if breathing is difficult. 
Remove and isolate contaminated clothing and shoes. 

In case of contact with substance, wipe from skin immediately; flush skin or eyes with running water for at least 20 minutes. 
Keep victim calm and warm.

Fire Fighting of Lithium amide:
DO NOT USE WATER OR FOAM. (FOAM MAY BE USED FOR CHLOROSILANES, SEE BELOW). 

SMALL FIRE: 
Dry chemical, soda ash, lime or sand. 

LARGE FIRE: 
DRY sand, dry chemical, soda ash or lime or withdraw from area and let fire burn. 
FOR CHLOROSILANES, DO NOT USE WATER; use AFFF alcohol-resistant medium-expansion foam.

DO NOT USE dry chemicals, soda ash or lime on chlorosilane fires (large or small) as they may release large quantities of hydrogen gas that may explode. 
If Lithium amide can be done safely, move undamaged containers away from the area around the fire. 

FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: 
Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. 
Cool containers with flooding quantities of water until well after fire is out. 

Do not get water inside containers. 
Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. 
ALWAYS stay away from tanks engulfed in fire.

Fire Fighting Procedures of Lithium amide:

If material on fire or involved in fire: 
Do not use water. 
Use graphite, soda ash or powdered sodium chloride, or suitable dry powder. 

If fire is massive, back off, protect surroundings, and let burn. 
Keep run-off water out of sewers and water sources.

Accidental Release Measures of Lithium amide:

IMMEDIATE PRECAUTIONARY MEASURE: 
Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. 

SPILL: 
Increase the immediate precautionary measure distance, in the downwind direction, as necessary. 

FIRE: 
If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

Cleanup Methods of Lithium amide:

Environmental considerations - land spill: 
Dig a pit, pond, lagoon, holding area to contain liquid or solid material. 
If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner.
Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.

Environmental considerations - water spill: 
Use natural barriers or oil spill control booms to limit spill travel Neutralize with dilute acid.

Disposal Methods of Lithium amide:
The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 
Recycle any unused portion of Lithium amide for Lithium amide approved use or return Lithium amide to the manufacturer or supplier. 

Ultimate disposal of the chemical must consider:
Lithium amide's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive Measures of Lithium amide:

If material not on fire and not involved in fire: 
Keep sparks, flames, and other sources of ignition away. 
Keep material out of water sources and sewers. 

Do not use water. 
Cover all suspected material with dry sand or earth to prevent ignition until material can be permanently disposed of.

Personnel protection Keep upwind. 
Avoid breathing dusts, and fumes from burning material.

The scientific literature for the use of contact lenses in industry is conflicting. 
The benefit or detrimental effects of wearing contact lenses depend not only upon Lithium amide, but also on factors including the form of Lithium amide, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. 

However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. 
In those specific cases, contact lenses should not be worn. 
In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Identifiers of Lithium amide:
CAS Number: 7782-89-0
ChemSpider: 22939
ECHA InfoCard: 100.029.062
PubChem CID: 24532
UNII: 7393OMU9LK
CompTox Dashboard (EPA): DTXSID7064815
InChI: InChI=1S/Li.H2N/h;1H2/q+1;-1
Key: AFRJJFRNGGLMDW-UHFFFAOYSA-N
InChI=1/Li.H2N/h;1H2/q+1;-1
Key: AFRJJFRNGGLMDW-UHFFFAOYAO
SMILES: [Li+].[NH2-]

Linear Formula: LiNH2
CAS Number: 7782-89-0
Molecular Weight: 22.96
EC Number: 231-968-4
MDL number: MFCD00011093
PubChem Substance ID: 24852671
NACRES: NA.22

Linear Formula: LiNH2
MDL Number: MFCD00011093
EC No.: 231-968-4
Beilstein/Reaxys No.: N/A
Pubchem CID: 24532
IUPAC Name: lithium; azanide
SMILES: [Li+].[NH2-]
InchI Identifier: InChI=1S/Li.H2N/h;1H2/q+1;-1
InchI Key: AFRJJFRNGGLMDW-UHFFFAOYSA-N

CAS: 7782-89-0
MDL Number: MFCD00011093
InChI Key: AFRJJFRNGGLMDW-UHFFFAOYSA-N
PubChem CID: 24532
IUPAC Name: lithium;azanide
SMILES: [Li+].[NH2-]

Properties of Lithium amide:
Chemical formula: LiNH2
Molar mass: 22.96 g·mol−1
Appearance: white solid
Density: 1.178 g/cm3
Melting point: 375 °C (707 °F; 648 K)
Boiling point: 430 °C (806 °F; 703 K) decomposes
Solubility in water: reacts
Solubility: slightly soluble in ethanol insoluble in ammonia

Compound Formula: H2LiN
Molecular Weight: 22.96
Appearance: White crystalline powder
Melting Point: 375 °C
Boiling Point: N/A
Density: 1.18 g/cm3
Solubility in H2O: Reacts violently
Exact Mass: 23.034729
Monoisotopic Mass: 23.034729

Quality Level: 200
Assay: 95%
Form: powder
mp: 380-400 °C
Density: 1.178 g/mL at 25 °C (lit.)
Greener alternative category: Enabling
SMILES string: [Li].CN
InChI: 1S/Li.H2N/h;1H2/q+1;-1
InChI key: AFRJJFRNGGLMDW-UHFFFAOYSA-N

Physical State Powder: Solid
Appearance: Light grey
Odor: Ammonia-like
Melting Point/Range: 373 °C / 703.4 °F
Boiling Point/Range: 430 °C / 806 °F @ 760 mmHg
Water: Solubility vigorous reaction
Density / Specific Gravity: 1.170

Molecular Weight: 23.0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 23.03472750
Monoisotopic Mass: 23.03472750
Topological Polar Surface Area: 1 Ų
Heavy Atom Count: 2
Complexity: 2
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 2
Compound Is Canonicalized: Yes

Specifications of Lithium amide:
Boiling Point: 430°C
Melting Point: 373°C
Color: White through Gray
Physical Form: Fine Powder
Quantity: 100 g
Assay Percent Range: 94% min. (LiNH2)
Molecular Formula: H2LiN
Linear Formula: LiNH2
Fieser: 01,600; 03,178; 05,392; 13,159; 17,311
Merck Index: 15, 5578
Solubility Information: Solubility in water: vigorous reaction. 
Other solubilities: forming lioh and nh3,insoluble in anhydr. ether,benzene and toluene
Molecular Weight (g/mol): 22.95
Formula Weight: 22.95
Percent Purity: 95%
Packaging: Glass bottle
Specific Gravity: 1.17
Density: 1.1700g/mL
Chemical Name or Material: Lithium amide, 95%

Thermochemistry of Lithium amide:
Std enthalpy of formation (ΔfH⦵298): -182 kJ/mol

Names of Lithium amide:

IUPAC name:
Lithium amide

Other names:
Lithium azanide
Lithamide

Synonyms of Lithium amide:
lithium amide
lithamide
lithium amide li nh2
lithiumamide
unii-7393omu9lk
lithium azanide
hsdb 649
linh2
lithium amide 25g
lithium amide
powder
LITHIUM AMIDE
7782-89-0
Lithamide
lithium;azanide
Lithium amide (Li(NH2))
7393OMU9LK
Lithiumamide
lithium azanide
MFCD00011093
UNII-7393OMU9LK
HSDB 649
EINECS 231-968-4
LiNH2
LITHIUM AMIDE [MI]
LITHIUM AMIDE [HSDB]
Lithium amide, powder, 95%
DTXSID7064815
Lithium amide, hydrogen-storage grade
AKOS030228593
FT-0627889
Q2565173
231-968-4 [EINECS]
7393OMU9LK
7782-89-0 [RN]
Amidure de lithium [French]
Azanide de lithium [French] [ACD/IUPAC Name]
LiNH2 [Formula]
Lithium amide [Wiki]
Lithium azanide [ACD/IUPAC Name]
Lithiumamid [German]
Lithiumazanid [German] [ACD/IUPAC Name]
Амид лития [Russian]
氨基锂 [Chinese]
12135-17-0 [RN]
553-54-8 [RN]
EINECS 231-968-4
Lithamide
lithium and azanide
lithium;azanide
Lithiumamide
MFCD00011093 [MDL number]
UNII:7393OMU9LK
UNII-7393OMU9LK